Mansion holiday rentals in Siesta Key
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Top-rated mansion rentals in Siesta Key
Guests agree: these mansions are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Siesta Key mansion rentals
Luxury mansion rentals
Home in Nokomis
4.88 out of 5 average rating, 147 reviews4/2.5 Oak Bahay, Heated Pool! 5min to Beach,4Acres
23–30 Dec
Home in Bradenton
4.91 out of 5 average rating, 158 reviewsHeated Saltwater Pool near Anna Maria Is.- 6bd/3ba
12–19 Jul
Home in Sarasota
4.79 out of 5 average rating, 85 reviews*Full Bay View Beauty, Private Heated Pool *
11–18 Dec
Home in Sarasota
4.96 out of 5 average rating, 23 reviewsNomadic Abode - heated salt water pool!
19–26 Aug
Home in Siesta Key
5.0 out of 5 average rating, 4 reviewsWater Front Private Villa, Luxury, Pool & Hottub
14–21 Oct
Home in Anna Maria
5.0 out of 5 average rating, 28 reviewsAmie House Chef’s kitchen Fun pool - walk to beach
20–27 Oct
Home in Siesta Key
5.0 out of 5 average rating, 13 reviewsBeautiful House with Heated pool
3–10 Dec
Home in Siesta Key
5.0 out of 5 average rating, 25 reviews4BR onSiesta Key Heated Pool Home - 1mile to beach
25 May – 1 Jun
Pet-friendly mansion rentals
Home in Holmes Beach
4.97 out of 5 average rating, 124 reviewsTwin Palms: Big House Steps to Beach w/Lush Pool
31 Aug – 7 Sep
Home in Bradenton
4.91 out of 5 average rating, 113 reviewsParadise Oasis w/ amazing pool | Near AMI beaches
7–14 Sep
Home in Sarasota
4.91 out of 5 average rating, 186 reviewsModern private getaway heated pool with spa
21–28 Sep
Home in Bradenton
4.99 out of 5 average rating, 132 reviewsBradenton Gem - BRAND NEW POOL!
13–20 Aug
Home in Bradenton
4.95 out of 5 average rating, 104 reviewsSpa & Pool+By The River+Near Beaches+Gameroom
15–22 Jan
Home in Sarasota
4.97 out of 5 average rating, 58 reviewsRenovated Ranch near Downtown Sarasota and Siesta
6–13 Oct
Home in Sarasota
5.0 out of 5 average rating, 17 reviewsCoastal Contemporary Pool Home
5–12 Dec
Home in Siesta Key
4.91 out of 5 average rating, 46 reviewsPet friendly Home- Blocks from Siesta Key Beach
20–27 Sep
Mansion rentals with a pool
Home in Sarasota
4.96 out of 5 average rating, 143 reviewsModern Luxury Home with heated pool in Sarasota.
8–15 Oct
Home in Sarasota
5.0 out of 5 average rating, 13 reviewsWaterside Villa - 4BD/2BA with a heated pool
10–17 Oct
Home in Sarasota
5.0 out of 5 average rating, 26 reviewsFamily friendly with large pool
6–13 Oct
Home in Sarasota
5.0 out of 5 average rating, 11 reviewsPool + Near Beach + Outdoor Games + Close to DT
5–12 Dec
Home in Sarasota
4.93 out of 5 average rating, 59 reviewsHeated Pool - Just 1 mile to Beach! Updated/Fun!
9–16 Dec
Home in Sarasota
5.0 out of 5 average rating, 28 reviewsFamily Fun House near Siesta Key Beach
24–31 Mar
Home in Ellenton
5.0 out of 5 average rating, 23 reviewsThe Pink Riverhouse- Free beach parking in PAG
14–21 Jun
Home in Sarasota
4.96 out of 5 average rating, 53 reviewsMinutes to Siesta Key, heated pool & tiki on water
27 Nov – 4 Dec
Destinations to explore
- Sarasota Holiday rentals
- Anna Maria Island Holiday rentals
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